Cinnarizine
N07C - Antivertigo preparations
ATC N07CA02
Small molecule
Oral
Natural product
JFDA label: Vertizin - 25mg tablets
Mechanism of Action
Blocker of Voltage-gated L-type calcium channel — Voltage-gated L-type calcium channel blocker; Antagonist of Histamine H1 receptor — Histamine H1 receptor antagonist
| Target | Action | Gene / class |
|---|---|---|
| Histamine H1 receptor efficacy | ANTAGONIST | HRH1 |
| Voltage-gated L-type calcium channel efficacy | BLOCKER |
Indications
Approved
- Vertigo — Vertigo
Pregnancy & Lactation
Pregnancy
Lactation
No Data
Hale L3
Expert opinion recommends that cinnarizine not be used in migraine prophylaxis in nursing mothers.[ 1 - 3 ] An alternate drug is preferred, especially while nursing a newborn or preterm infant.
Chemistry & Properties
| Formula | C26H28N2 |
|---|---|
| Molecular weight | 368.52 g/mol |
| IUPAC name | 1-benzhydryl-4-[(E)-3-phenylprop-2-enyl]piperazine |
| CAS | 298-57-7 |
| PubChem CID | 1547484 |
| InChIKey | DERZBLKQOCDDDZ-JLHYYAGUSA-N |
| logP | 5.11 (XLogP 5.8) |
| Polar surface area | 6.48 Ų |
| H-bond acceptors / donors | 2 / 0 |
| Drug-likeness (QED) | 0.60 |
| Lipinski violations | 1 |
SMILES
C(=C/c1ccccc1)\CN1CCN(C(c2ccccc2)c2ccccc2)CC1Biology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | Yes |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP1A2 | Inhibitor | — |
| CYP1A2 | Substrate | — |
| CYP2B6 | Inhibitor | — |
| CYP2B6 | Substrate | — |
| CYP2C19 | Substrate | — |
| CYP2C8 | Inhibitor | — |
| CYP2C9 | Inhibitor | — |
| CYP2C9 | Substrate | — |
| CYP2D6 | Inhibitor | — |
| CYP2D6 | Substrate | — |
Receptor binding (top 1)
| Target | Action | Affinity |
|---|---|---|
| HISTAMINE H4 (HRH4) | Binding | pKi 6.8 |
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)MDR1 (Substrate)P-gp (Substrate)
Registered Products (13)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Cinar Tab | Tablet 25 mg | 30 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 1.000 |
| Vertizin - | Tablet 25 mg | 30 tab pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 1.020 |
| Vertizin- | Capsule 75 mg | 20 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 1.700 |
| Cinar forte Tab | Tablet 75 mg | 20 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 1.940 |
| Cinar forte Tab | Tablet 75 mg | 30 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 2.880 |
| Vertalix 20mg/40mg Tablets | Tablet Cinnarizine 20 mg, Dimenhydrinate 40 mg | 20 tab | Misk Pharmaceutical Industries Co.` | 9.740 |
| Azalonum 20mg/40 mg Tablet | Tablet 20 mg, 40 mg | 20 tab | Khoury Drug Store | 10.820 |
| Cinar Tab | Tablet 25 mg | 500 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 14.500 |
| Vertizin - | Tablet 25 mg | 500 tab pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 14.790 |
| Vertizin- | Tablet 25 mg | 1000 tab pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 28.000 |
| Cinar forte Tab | Tablet 75 mg | 500 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 37.580 |
| Vertizin- | Capsule 75 mg | 1000 cap pack varies | AL-RAM PHARMA.INDUS.CO.LTD/JORDAN | 72.250 |
| Cinar forte Tab | Tablet 75 mg | 1000 tab pack varies | Hayat Pharmaceutical Industries CO.PLC/JORDAN | 82.450 |